路易斯酸催化的碳氢键官能团化反应构建氧化吲哚结构的研究
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摘要
近十多年来,过渡金属催化的碳氢键活化反应研究已经成为最富有前景和希望的新课题。对环境友好的,温和的C-H键活化反应将是构建C-X (X=C, N, O等)键的最理想手段,是最具有原子经济性的、简捷高效地合成有机分子的方法。无疑,这将是未来二十年最有竞争力的催化化学研究领域之一。因而,深入研究C-H键活化与断裂的基本规律,不仅具有重要的学术意义,而且有潜在的巨大实用价值。美国科学杂志曾就C-H键活化发表了专门评论,将其称为金属有机化学的“圣碑”。
在我攻读博士期间,有幸在杨尚东教授及梁永民教授的研究小组参与了路易斯酸催化的直接碳氢键转化成碳碳键的反应研究,合成了一系列氧化吲哚结构单元的化合物。论文主要包括以下几个部分：
第一章主要对过渡金属催化的分解重氮化合物生成卡宾的C-H键插入反应研究以及在全合成中的应用进行了归纳和总结。
第二章详细阐述了三氟甲烷磺酸银(AgOTf)催化的分解重氮化合物生成卡宾,对芳基碳氢键直接插入构建烯基氧化吲哚类化合物的反应。该反应的催化体系非常简单,环境友好,避免了使用碱,氧化剂,或者其它的添加剂；NMR, X-ray,DFT计算表明3-烯基氧化吲哚是唯一的产物；除此之外,实验数据和DFT计算表明：银催化剂作为路易斯酸促进形成自由卡宾并且该反应的决速步是N2的释放。
第三章主要对过渡金属催化的碳氢键对不饱和碳杂键的加成反应研究进行了综述。
第四章阐述了三氟甲烷磺酸钪(Sc(OTf)3)催化的分子内芳基碳氢键直接对α-酰胺酮的加成构建3-羟基氧化吲哚类化合物的反应。与传统的方法(有机金属试剂或者富电子试剂对靛红的加成,以及分子内的芳基卤代物对α-酰胺酮的加成反应)相比较,该方法简单易行,环境友好,省去了制备有机金属试剂或者卤代物的繁琐过程。
In the past decade, transition metal catalyzed C-H bond activation reactions have emerged as promising new catalytic transformations. Environmentally friendly, mild C-H bond activation reaction will became the ideal means to build a C-X bond (X=C, N, O, etc.), which is most atom economy, simplely and efficiently method for synthesis of organic molecules. Undoubtedly, this will be the most competitive research fields of catalytic chemistry in the next two decades. Thus, in-depth study of the basic law of the C-H bond activation and cleavage, not only has the important academic significance, but also has a huge potential practical value. Scientific American magazine has been published a C-H bond activation specifically comment and considered it as the "holy grail" of organometallic chemistry.
During my PhD, I had the great honor involved in the research groups of Professor Shang-Dong Yang and Professor Yong-Min Liang to study on new methods of lewis acid-catalyzed direct conversion of aromatic rings carbons hydrogen bonds into carbon-carbon bonds to form oxindoles structure motif.
This thesis includes the following:
In first chapter, recent studies about transition-metal-catalyzed reaction of diazo compounds generates metal carbene or carbenoid intermediates that undergo catalytic C-H bond insertion reactions and their application of total synthesis are reviewed.
In second chapter, A novel protocol for the preparation of various oxindoles via a silver-catalyzed carbene insertion to aromatic C-H bond has been developed. The process is simple, environmentally conscious, and avoids the use of bases, oxidants, or other additives. All analyses including NMR, single crystal X-ray, and DFT calculations show that the3-methyleneoxindole is obtained as a single product. In addition experiments and computational analysis illustrated that silver prompt the formation of a free carbene and the rate-determining step of the catalytic cycle is N2dissociation.
In third chapter, recent developments of transition metal catalyzed direct nucleophilic addition of C-H bonds in hydrocarbons and their derivatives to the unsaturated carbon-heteroatom to produce addition product are reviewed.
In four chapter, A novel method for Sc(OTf)3-catalyzed intramolecular Friedel-Crafts alkylation to construct3-hydroxy-2-oxindoles by direct C-H addition to a-ketoanilides has been developed. In comparision with traditional methods of nucleophilic conjugate additions of organometallic reagents or electron-rich reagents to isatins and intramolecular addition of aryl chlorides to ketoamides. This protocol is simple, environmentally conscious, and omits the complicated preparation of organometallic reagents or halogenations procedures.
在我攻读博士期间,有幸在杨尚东教授及梁永民教授的研究小组参与了路易斯酸催化的直接碳氢键转化成碳碳键的反应研究,合成了一系列氧化吲哚结构单元的化合物。论文主要包括以下几个部分：
第一章主要对过渡金属催化的分解重氮化合物生成卡宾的C-H键插入反应研究以及在全合成中的应用进行了归纳和总结。
第二章详细阐述了三氟甲烷磺酸银(AgOTf)催化的分解重氮化合物生成卡宾,对芳基碳氢键直接插入构建烯基氧化吲哚类化合物的反应。该反应的催化体系非常简单,环境友好,避免了使用碱,氧化剂,或者其它的添加剂；NMR, X-ray,DFT计算表明3-烯基氧化吲哚是唯一的产物；除此之外,实验数据和DFT计算表明：银催化剂作为路易斯酸促进形成自由卡宾并且该反应的决速步是N2的释放。
第三章主要对过渡金属催化的碳氢键对不饱和碳杂键的加成反应研究进行了综述。
第四章阐述了三氟甲烷磺酸钪(Sc(OTf)3)催化的分子内芳基碳氢键直接对α-酰胺酮的加成构建3-羟基氧化吲哚类化合物的反应。与传统的方法(有机金属试剂或者富电子试剂对靛红的加成,以及分子内的芳基卤代物对α-酰胺酮的加成反应)相比较,该方法简单易行,环境友好,省去了制备有机金属试剂或者卤代物的繁琐过程。
In the past decade, transition metal catalyzed C-H bond activation reactions have emerged as promising new catalytic transformations. Environmentally friendly, mild C-H bond activation reaction will became the ideal means to build a C-X bond (X=C, N, O, etc.), which is most atom economy, simplely and efficiently method for synthesis of organic molecules. Undoubtedly, this will be the most competitive research fields of catalytic chemistry in the next two decades. Thus, in-depth study of the basic law of the C-H bond activation and cleavage, not only has the important academic significance, but also has a huge potential practical value. Scientific American magazine has been published a C-H bond activation specifically comment and considered it as the "holy grail" of organometallic chemistry.
During my PhD, I had the great honor involved in the research groups of Professor Shang-Dong Yang and Professor Yong-Min Liang to study on new methods of lewis acid-catalyzed direct conversion of aromatic rings carbons hydrogen bonds into carbon-carbon bonds to form oxindoles structure motif.
This thesis includes the following:
In first chapter, recent studies about transition-metal-catalyzed reaction of diazo compounds generates metal carbene or carbenoid intermediates that undergo catalytic C-H bond insertion reactions and their application of total synthesis are reviewed.
In second chapter, A novel protocol for the preparation of various oxindoles via a silver-catalyzed carbene insertion to aromatic C-H bond has been developed. The process is simple, environmentally conscious, and avoids the use of bases, oxidants, or other additives. All analyses including NMR, single crystal X-ray, and DFT calculations show that the3-methyleneoxindole is obtained as a single product. In addition experiments and computational analysis illustrated that silver prompt the formation of a free carbene and the rate-determining step of the catalytic cycle is N2dissociation.
In third chapter, recent developments of transition metal catalyzed direct nucleophilic addition of C-H bonds in hydrocarbons and their derivatives to the unsaturated carbon-heteroatom to produce addition product are reviewed.
In four chapter, A novel method for Sc(OTf)3-catalyzed intramolecular Friedel-Crafts alkylation to construct3-hydroxy-2-oxindoles by direct C-H addition to a-ketoanilides has been developed. In comparision with traditional methods of nucleophilic conjugate additions of organometallic reagents or electron-rich reagents to isatins and intramolecular addition of aryl chlorides to ketoamides. This protocol is simple, environmentally conscious, and omits the complicated preparation of organometallic reagents or halogenations procedures.
引文
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